Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010620/cm6008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010620/cm6008Isup2.hkl |
CCDC reference: 189908
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.002 Å
- R factor = 0.028
- wR factor = 0.079
- Data-to-parameter ratio = 13.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.646 0.862 Tmin' and Tmax expected: 0.833 0.956 RR' = 0.861 Please check that your absorption correction is appropriate. General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.109 Tmax scaled 0.956 Tmin scaled 0.717
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C5H6N+·C10H8N2PS2− | F(000) = 688 |
Mr = 331.38 | Dx = 1.437 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 11.6700 (18) Å | Cell parameters from 7150 reflections |
b = 11.930 (3) Å | θ = 2.4–27.0° |
c = 11.108 (3) Å | µ = 0.45 mm−1 |
β = 98.005 (18)° | T = 183 K |
V = 1531.4 (5) Å3 | Plate, yellow |
Z = 4 | 0.40 × 0.30 × 0.10 mm |
Bruker SMART three-circle diffractometer [OK?] | 3331 independent reflections |
Radiation source: fine-focus sealed tube | 2764 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan (North et al., 1968) | h = −14→14 |
Tmin = 0.646, Tmax = 0.862 | k = −15→15 |
24788 measured reflections | l = −14→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.079 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.05P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3 |
3331 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Experimental. There is only one resonance in the 31P NMR spectrum of the title compound (98.0 p.p.m., 85% H3PO4 was used as a standard). Characteristic vibrations were identified in the IR spectrum of the reaction product: NH-bond (3174 cm-1), CH bonds (3102, 3076, 3058, 3026, 2729, 2672 cm-1) and P═S bond (650–750 cm-1). These values are in agreement with the proposed structure. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 I>2σ(I)(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
P | −0.00648 (3) | 0.34204 (3) | 0.10643 (3) | 0.02226 (10) | |
S1 | −0.10702 (3) | 0.44896 (3) | 0.18207 (4) | 0.02998 (11) | |
S2 | −0.08603 (3) | 0.25960 (3) | −0.03473 (4) | 0.02970 (11) | |
N1 | 0.11751 (10) | 0.40119 (11) | 0.07569 (12) | 0.0267 (3) | |
H1N | 0.1185 (16) | 0.4429 (16) | 0.0169 (19) | 0.043 (5)* | |
N2 | 0.06916 (11) | 0.26046 (10) | 0.21474 (12) | 0.0251 (3) | |
H2N | 0.0395 (16) | 0.2376 (14) | 0.2697 (18) | 0.030 (5)* | |
C1 | 0.21753 (12) | 0.35782 (11) | 0.14134 (13) | 0.0219 (3) | |
C2 | 0.32980 (13) | 0.38618 (12) | 0.13501 (13) | 0.0249 (3) | |
H2 | 0.3483 (15) | 0.4425 (14) | 0.0790 (16) | 0.032 (4)* | |
C3 | 0.42046 (12) | 0.33272 (12) | 0.21349 (13) | 0.0248 (3) | |
C4 | 0.53880 (13) | 0.35772 (13) | 0.21026 (15) | 0.0302 (3) | |
H4 | 0.5591 (14) | 0.4120 (14) | 0.1515 (15) | 0.030 (4)* | |
C5 | 0.62486 (14) | 0.30543 (15) | 0.28703 (15) | 0.0336 (4) | |
H5 | 0.6987 (16) | 0.3233 (14) | 0.2824 (16) | 0.034 (5)* | |
C6 | 0.59696 (14) | 0.22550 (14) | 0.37127 (16) | 0.0343 (4) | |
H6 | 0.6574 (16) | 0.1896 (14) | 0.4230 (17) | 0.036 (5)* | |
C7 | 0.48318 (13) | 0.19927 (14) | 0.37653 (15) | 0.0309 (3) | |
H7 | 0.4632 (16) | 0.1438 (15) | 0.4319 (17) | 0.038 (5)* | |
C8 | 0.39203 (13) | 0.25143 (12) | 0.29864 (13) | 0.0250 (3) | |
C9 | 0.27364 (13) | 0.22423 (12) | 0.30422 (14) | 0.0243 (3) | |
H9 | 0.2548 (13) | 0.1716 (13) | 0.3613 (15) | 0.024 (4)* | |
C10 | 0.18925 (12) | 0.27584 (11) | 0.22662 (13) | 0.0223 (3) | |
N3 | 0.12713 (16) | 0.51061 (15) | 0.35748 (18) | 0.0513 (5) | |
H3N | 0.068 (2) | 0.510 (2) | 0.312 (2) | 0.072 (8)* | |
C11 | 0.1432 (2) | 0.45051 (17) | 0.4613 (3) | 0.0606 (7) | |
H11 | 0.087 (2) | 0.413 (2) | 0.479 (3) | 0.095 (9)* | |
C12 | 0.2477 (2) | 0.45281 (17) | 0.5322 (2) | 0.0552 (6) | |
H12 | 0.268 (2) | 0.415 (2) | 0.604 (3) | 0.085 (8)* | |
C13 | 0.33487 (18) | 0.51536 (16) | 0.49544 (17) | 0.0448 (4) | |
H13 | 0.4124 (19) | 0.5174 (17) | 0.545 (2) | 0.059 (6)* | |
C14 | 0.31582 (18) | 0.57502 (16) | 0.39022 (18) | 0.0438 (4) | |
H14 | 0.3749 (19) | 0.6195 (19) | 0.361 (2) | 0.064 (6)* | |
C15 | 0.21102 (19) | 0.57213 (16) | 0.32180 (18) | 0.0463 (5) | |
H15 | 0.1928 (19) | 0.6162 (19) | 0.247 (2) | 0.065 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P | 0.02083 (19) | 0.02580 (19) | 0.02035 (19) | 0.00149 (14) | 0.00353 (14) | 0.00430 (14) |
S1 | 0.0315 (2) | 0.0328 (2) | 0.0274 (2) | 0.00757 (16) | 0.01034 (16) | 0.00468 (15) |
S2 | 0.0275 (2) | 0.0357 (2) | 0.0247 (2) | −0.00089 (15) | −0.00071 (15) | 0.00002 (15) |
N1 | 0.0230 (6) | 0.0313 (7) | 0.0262 (7) | 0.0000 (5) | 0.0042 (5) | 0.0113 (5) |
N2 | 0.0205 (6) | 0.0318 (7) | 0.0231 (7) | −0.0012 (5) | 0.0037 (5) | 0.0098 (5) |
C1 | 0.0243 (7) | 0.0233 (7) | 0.0184 (7) | −0.0002 (5) | 0.0037 (5) | −0.0006 (5) |
C2 | 0.0276 (7) | 0.0258 (7) | 0.0221 (7) | −0.0023 (6) | 0.0063 (6) | 0.0011 (6) |
C3 | 0.0241 (7) | 0.0291 (7) | 0.0214 (7) | −0.0024 (6) | 0.0042 (6) | −0.0060 (6) |
C4 | 0.0272 (8) | 0.0360 (8) | 0.0280 (8) | −0.0058 (6) | 0.0061 (6) | −0.0039 (7) |
C5 | 0.0215 (8) | 0.0447 (9) | 0.0345 (9) | −0.0044 (7) | 0.0036 (6) | −0.0074 (7) |
C6 | 0.0236 (8) | 0.0441 (9) | 0.0331 (9) | 0.0035 (7) | −0.0033 (7) | −0.0031 (7) |
C7 | 0.0273 (8) | 0.0383 (8) | 0.0262 (8) | 0.0007 (7) | 0.0011 (6) | 0.0020 (7) |
C8 | 0.0244 (7) | 0.0295 (7) | 0.0208 (7) | −0.0001 (6) | 0.0017 (6) | −0.0034 (6) |
C9 | 0.0253 (7) | 0.0272 (7) | 0.0205 (7) | −0.0003 (6) | 0.0035 (6) | 0.0033 (6) |
C10 | 0.0221 (7) | 0.0247 (7) | 0.0204 (7) | −0.0021 (5) | 0.0042 (6) | −0.0018 (5) |
N3 | 0.0425 (10) | 0.0530 (10) | 0.0556 (11) | 0.0052 (8) | −0.0034 (9) | −0.0315 (9) |
C11 | 0.0657 (15) | 0.0400 (11) | 0.0846 (19) | −0.0197 (10) | 0.0407 (14) | −0.0206 (11) |
C12 | 0.0828 (17) | 0.0448 (11) | 0.0409 (11) | 0.0025 (11) | 0.0185 (11) | 0.0081 (9) |
C13 | 0.0497 (11) | 0.0484 (10) | 0.0353 (10) | 0.0055 (9) | 0.0021 (9) | −0.0064 (8) |
C14 | 0.0494 (11) | 0.0440 (10) | 0.0400 (11) | −0.0038 (9) | 0.0135 (9) | 0.0002 (8) |
C15 | 0.0609 (13) | 0.0458 (10) | 0.0318 (10) | 0.0108 (9) | 0.0056 (9) | −0.0026 (8) |
P—N1 | 1.6870 (13) | C6—H6 | 0.947 (18) |
P—N2 | 1.6966 (13) | C7—C8 | 1.418 (2) |
P—S2 | 1.9703 (6) | C7—H7 | 0.954 (19) |
P—S1 | 1.9960 (6) | C8—C9 | 1.429 (2) |
N1—C1 | 1.3874 (19) | C9—C10 | 1.362 (2) |
N1—H1N | 0.82 (2) | C9—H9 | 0.940 (16) |
N2—C10 | 1.4012 (18) | N3—C15 | 1.327 (3) |
N2—H2N | 0.79 (2) | N3—C11 | 1.348 (3) |
C1—C2 | 1.364 (2) | N3—H3N | 0.80 (3) |
C1—C10 | 1.4317 (19) | C11—C12 | 1.357 (4) |
C2—C3 | 1.424 (2) | C11—H11 | 0.84 (3) |
C2—H2 | 0.960 (17) | C12—C13 | 1.369 (3) |
C3—C4 | 1.418 (2) | C12—H12 | 0.92 (3) |
C3—C8 | 1.426 (2) | C13—C14 | 1.360 (3) |
C4—C5 | 1.373 (2) | C13—H13 | 0.99 (2) |
C4—H4 | 0.972 (17) | C14—C15 | 1.347 (3) |
C5—C6 | 1.406 (2) | C14—H14 | 0.96 (2) |
C5—H5 | 0.896 (18) | C15—H15 | 0.98 (2) |
C6—C7 | 1.373 (2) | ||
N1—P—N2 | 90.41 (6) | C6—C7—C8 | 121.44 (16) |
N1—P—S2 | 111.72 (5) | C6—C7—H7 | 120.7 (11) |
N2—P—S2 | 114.77 (5) | C8—C7—H7 | 117.9 (11) |
N1—P—S1 | 112.89 (5) | C7—C8—C3 | 118.63 (14) |
N2—P—S1 | 110.27 (5) | C7—C8—C9 | 121.43 (14) |
S2—P—S1 | 114.49 (3) | C3—C8—C9 | 119.93 (13) |
C1—N1—P | 114.85 (10) | C10—C9—C8 | 119.22 (14) |
C1—N1—H1N | 122.6 (14) | C10—C9—H9 | 120.8 (10) |
P—N1—H1N | 121.4 (14) | C8—C9—H9 | 120.0 (10) |
C10—N2—P | 113.98 (10) | C9—C10—N2 | 128.75 (14) |
C10—N2—H2N | 120.8 (13) | C9—C10—C1 | 120.96 (13) |
P—N2—H2N | 120.3 (13) | N2—C10—C1 | 110.29 (12) |
C2—C1—N1 | 128.61 (13) | C15—N3—C11 | 121.93 (19) |
C2—C1—C10 | 121.00 (13) | C15—N3—H3N | 115.1 (19) |
N1—C1—C10 | 110.36 (12) | C11—N3—H3N | 122.9 (19) |
C1—C2—C3 | 119.61 (14) | N3—C11—C12 | 119.5 (2) |
C1—C2—H2 | 120.7 (10) | N3—C11—H11 | 118 (2) |
C3—C2—H2 | 119.6 (10) | C12—C11—H11 | 123 (2) |
C4—C3—C2 | 122.23 (14) | C11—C12—C13 | 118.9 (2) |
C4—C3—C8 | 118.50 (14) | C11—C12—H12 | 126.3 (16) |
C2—C3—C8 | 119.27 (13) | C13—C12—H12 | 114.8 (16) |
C5—C4—C3 | 121.28 (15) | C14—C13—C12 | 120.1 (2) |
C5—C4—H4 | 119.6 (10) | C14—C13—H13 | 119.5 (13) |
C3—C4—H4 | 119.1 (10) | C12—C13—H13 | 120.3 (13) |
C4—C5—C6 | 120.28 (15) | C15—C14—C13 | 119.88 (19) |
C4—C5—H5 | 118.8 (11) | C15—C14—H14 | 117.3 (13) |
C6—C5—H5 | 120.9 (11) | C13—C14—H14 | 122.8 (13) |
C7—C6—C5 | 119.86 (15) | N3—C15—C14 | 119.66 (19) |
C7—C6—H6 | 120.9 (11) | N3—C15—H15 | 117.8 (13) |
C5—C6—H6 | 119.2 (11) | C14—C15—H15 | 122.5 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···S1i | 0.82 (2) | 2.55 (2) | 3.3632 (15) | 172.3 (18) |
N3—H3N···S1 | 0.80 (3) | 2.44 (3) | 3.2127 (19) | 163 (2) |
Symmetry code: (i) −x, −y+1, −z. |
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